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June 23, 2021

Dating today is not for the faint of heart

Being single isn’t for wimps. It’s tough out there in the dating world. So tough, in fact, that I’ve found myself becoming more and more comfortable with my single status.

Don’t get me wrong. I’ve been in love and think fondly of the long-term relationships of my past. It’s the dating part that gets me. Or that I don’t get.

I’ve been set up on dates, given online dating a shot and even eyed – from a distance – one or two new faces that came through the door at the office.

But you just never know how a first – or even second – date is going to go until you’re in the moment.

I had a date once with a man who, when the bill came, said he didn’t have any cash and asked if I could foot the bill. I generally offer to pay for my portion anyway, so I simply paid the entirety. He called me for a second date the following week, to which I agreed, thinking perhaps he felt bad about the previous snafu. I realized how wrong I was when the bill came and we both sat looking at each other in silence, until he said, “I’ve been unemployed for months. Can you get this one, too?”

That detail fell through the cracks. I’m not one to pepper someone with reporter-type questions, so perhaps I never asked him, “What do you do?”

Maybe I should let my newspaper industry instincts take over more often.

Then there was the guy who I met on a “reputable” dating site. After talking on the phone several times, we decided to meet at a restaurant in San Jose. He was waiting outside the restaurant and after we greeted each other, he suggested we skip dinner and simply head over to the hotel room he’d rented for the evening. Let’s just say I made an early departure for home.

Along with my good qualities, I know I have flaws too – things a man might consider dealbreakers. And there have been plenty of times when I’ve been on the receiving end of “It was nice meeting you, but … ” when I thought the date was going well.

A man and I once took our dogs – my terrier and his bulldog – to a dog park on a casual get-to-know-you date. He clearly loved his dog, as I do mine, and the conversation was good. He asked if we could go out again, and we saw each other a few days later. When the phone calls stopped, I wished he’d simply said, “It was nice meeting you, but …”

Several months later I received a random text that he’d had some issues he needed to deal with but would like to see me again, if I was willing. He said he’d call to make plans for that weekend.

He never did.

And there was the friend of a friend who, at the end of our date, simply said he didn’t feel a connection. I appreciated his honesty – and his gentlemanly manner throughout the evening even though he wasn’t interested.

Honesty is a big deal. My 21-year-old self would have no doubt approached those dates differently, but my priorities have changed through the years. Unemployed? Let me know. People fall on hard times and it’s not a dealbreaker. Just don’t keep it quiet with the expectation of a couple of free meals. Not feeling it? That’s OK, too. I’d rather we be honest – but polite – with each other and not waste time by stringing it along.

Admittedly, sometimes I have to remind myself that there still are some good ones left. And I have a few close (and married) friends who occasionally smack me upside the head when I get down on myself and tell me that singlehood isn’t the worst thing that could happen.

Sure, I’d love to be done with dating and meet someone with whom I connect, but I really am doing OK. I have a job I enjoy, have traveled to various parts of the globe and have gained a level of independence that some never do.

The worst part about being single at my age is when people – usually extended family members – ask, “When are you going to meet someone and tie the knot?”

Someday soon? Never?

I wish I knew. But in the meantime, I’ll continue my dating adventures in hopes of finding a real connection, knowing that, in the end, I’m going to be just fine.

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